Chapter 19
On Tuesday morning Jake woke with another groan, the fabric of his sheets feeling so intense on his smooth skin reminding him of his predicament. While it felt kind of good, he hated it nevertheless, it was after all a source of so much trouble and a clear sign of Valeria’s control over him. Unlike yesterday however he actually brightened up a little as he became more clearheaded. These were his final moments under Valeria’s thumb, the moment she unlocked him before practice, he would finally be free of her no matter which rumours she threatened to spread. It would be word against word and with his announcements for the women’s team before every match he could reasonably say that he had even honoured their wager. All people would know was that he had succeeded at bedding Valeria, sure they would know he had acted like a complete wimp for it, but he could spin it that that had all been part of the plan. As soon as that cage came off before practice he was free, Jake thought with a smile.
As he went over his morning routine he was even happy to put on those white satin panties he had worn before getting this frilly lingerie. He had grown kind of used to the slick fabric on his smooth skin, it felt embarrassingly good, and he was more than happy for the lack of colour, frills or that annoying bit of fabric that rode up his ass with those thongs. As far as panties went, these weren’t so bad he had learned. Not having to wear stockings was also great, one less thing that could be discovered, especially since he had neglected to clean up his matte stockings leaving him only with the slightly glossy ones to wear. Plus he wouldn’t be able to ruin them and potentially have to go to the store for more, not that that was happening, hell he hadn’t bother to wash what he had worn yesterday simply because it didn’t matter anymore, he would be free before Valeria could check and then he could get rid of all of this entirely.
Feeling better and more confident already Jake went off to class with a smile. With these white panties he was not nearly as concerned about discovery anymore, no one had known in the week he had worn them and Valeria had been right, a quick glimpse of white underwear wouldn’t be too hard to explain even though that was pretty much impossible since he wore them under his boxers like always. If he had been able to go unnoticed with those frilly thongs and stockings, these wouldn’t pose much of a problem, he was sure of that much.
At college things only continued to get better as well. There was the usual teasing about how much he put up with for Valeria, but he just answered those with the same responses that it was worth it. He still had to stay low, call Valeria Miss and all that, but with him in just those boring panties as she had called him she seemed less eager to tease and torment him. They just didn’t seem to excite her as much. It was still embarrassing for Jake to let her check, but he was able to counter her disappointment over not wearing the exciting lingerie with being scared for practice which was the whole reason Valeria had allowed him to go with just these panties so she couldn’t really do more about it than voice her disappointment. Acting low for a little longer was so much easier now that the end was near and he got less teasing.
Finally as their last class finished and he had a quick meal at the cafeteria, the moment he had been waiting for ever since the plan had hatched arrived. Going to the locker rooms he made a quick stop at the bathrooms in the sports building to meet with Valeria. It hadn’t gone unnoticed that Jake had been acting kind of relieved all day and she could sense he was up to something. Given how this was the first time she would let him out of his cock cage without restraints after tricking him into the thing, it was pretty easy to guess just what he was up to, but she had given her word on unlocking him before practice if he was good, and he had been good. She wouldn’t go back on that now, besides she had plenty of evidence to blackmail him back in that cage if he decided to act stupid, which she kind of hoped he would, it was a nice test and a potential reason to accelerate her plans if he failed. She would have to wait and see, but right now she could still have some fun in the bathroom.
“So princess, I assume you came here to get that cage taken off before practice so you can keep on playing the tough athlete rather than the delicate panty lover you are, so the boys wouldn’t laugh at your locked up clitty is that right? Well you know what to do if you want out of that cage, kiss the key and ask me nicely to be set free. By the way you better hurry, cause I don’t want to be late for practice so I’m getting out of here whether you are out of that cage or not, I did after all promise to let you out if you were good, and good panty lovers follow orders quickly.” Valeria teased with a huge smirk as she pointed down at the key around her ankle.
All Jake could do was let out a sigh and drop to his knees, playing along with Valeria’s stupid game for one last time. He knew better than to hesitate and protest now as the last thing he wanted was to be stuck in this situation until the next practice, especially when he would potentially get in trouble over not having done his laundry, delaying things even more. Just thinking of this as a last indignity made it a lot easier to follow through with he thought as he placed a kiss right on the key, shuddering in shame as his lips touched Valeria’s warm nylon clad ankle above the rim of her sneaker. Looking back up at the broadly smirking Valeria he spoke. “Could you please unlock my cage Miss?” He hated how weak and submissive it made him feel, but this was the last time he told himself as he was about to stand back up.
Valeria was quick to smash his hope of this being over already though. Before he could truly get up Valeria quickly and utterly respectless placed her foot on his shoulder and pushed down, keeping him on his knees on the floor for the moment. “As promised I will panty lover, especially since you asked so nicely, now let me just rest my foot for a moment so I don’t need to lean all the way down for that key okay?” Valeria grinned as she slowly took the small key from her anklet right next to his face before finally getting her foot back down allowing the mortified soccer captain to get up.
“There we go babe, now why don’t you pull down your pants, lower your panties and let me take care of that cage of yours?” Valeria cooed, dragging this teasing torment out just a little longer. She just so loved having Jake following her orders and squirm under her control. It was not something she was willing to give up, especially not when he looked so cute once again exposing his panties and his bright pink cage with a blushing face that looked just as bright. She wasted no time taking the metal thing in her hands, lightly stroking her nails over his balls to get out a whimpering moan that seemed to turn his face an even deeper shade of red. Very pleased with herself she finally put the small key into the equally small lock and opened it up, taking the cage off his cock with a big grin as he instantly turned rock hard in her hand.
“Awww, it looks like our panty lover hasn’t lost his excitement over regular boring panties yet despite all the new cute lingerie. How cute! In any case we better get going now. As for your cage, come meet me right here after practice so I can put it back on. Be good and I will let you out for your next practice as well, be naughty and expected a punishment, now have fun.” Valeria smirked as she stashed the cage and the keys away while Jake hurried to pull his panties and pants back in place, if anything he wanted to strip out of these panties right here and now, but that would require taking everything from the waist down off and he wasn’t feeling that, he would just not put them on again after his shower he figured.
With the panties hidden from view once more giving him some confidence, paired with the fact that he was now finally free again Jake did find the confidence to tell Valeria off like he had been wanting to for a very long time. “Fuck you and your stupid rules bitch, I’m never doing a damn thing you say ever again and I’m definitely never letting you put me in that cage again. You can go to hell, no one will believe I actually put on any of that female garbage you made me wear and I’ve done some things that made it plausible enough that I followed through on the terms of our bet. You have no power over me bitch so fuck you.” He hissed at her, not wanting to scream as he didn’t want anyone passing by in the hall way to overhear, but he was happy to get his point across. As he turned on his heel and left he couldn’t quite feel relieved though. Despite feeling like he was free, he had been under Valeria’s control for so long that it somehow felt bad and scary to talk to her like that, not only that, but she had taken his whole tirade with a smirk rather than the shock he had been expecting. It just didn’t feel right, like he was in trouble or something.
Shaking his head Jake decided that that was probably just his imagination. He had thought this through and it would just be word against word. The most damning things would sound so far fetched that he could easily deny them without any harm to his reputation, he was free from her now, free forever Jake reminded himself as he occupied himself with thinking about the club tonight. Oh he would definitely go clubbing, hooking up with the first chick that caught his eye and fuck her silly all night long. Finally he would get to have some real sex again, real steaming hot sex rather than frustration, masturbation and embarrassing hand jobs. Damn he was looking forward to that. He had always liked sex, it had always been great, but he had never quite craved it like he did now after he had been without for so very long.
“Alright guys, who’s up for a party tonight? I just broke up with Valeria and I need a few drinks and a fucking amazing rebound. Guess I also owe you guys those rounds for crossing that name off the list.” Jake instantly shouted with big smile as he barged into the dressing room, quickly re-establishing his old image and starting to fix what damage had been done to his reputation among the guys and otherwise. He was a free man again and that called for a great celebration. He had always known crossing Valeria off his list would be a cause for a party, but he had never thought it would be this much cause for a party, that he would be left with so much catching up to do rather than left satisfied that he had finally bedded the women’s soccer captain. He might not have actually fucked her, but everyone thought he did which was what truly mattered.
Practice was amazing, for the first time in a long time Jake felt like he could go all out again, messing and throwing banter with his friends, but as good as it was to be free again, he could never feel completely at ease. Every time their eyes seemed to cross during practice Valeria gave him an ominous smile that was downright unsettling, it was probably nothing, it had to be nothing, still it didn’t allow him to feel completely at ease. Hopefully that feeling would soon eb away into nothingness over the coming few days as he would try to forget about all that had happened under Valeria’s rule.
Making some plans for the evening and talking about how he couldn’t wait to bang whichever chick he wanted in the dressing room after practice paired with he lack of Valeria’s practice certainly helped him forget about his last couple of weeks a little. Getting dressed in just boxers was also great, at least for his confidence and self-esteem as he did have to admit that the satin of the panties felt way better than the coarse in comparison cotton of his boxers did. Then again, that slick satin was one of the main reasons he felt exposed wearing panties, the soft caresses reminding him constantly of what he was wearing so if anything he was glad to be rid of them.
As much as he didn’t want anything to do with those panties anymore he still ended up stuffing them in his bag, after all he still couldn’t afford anyone finding them and starting to ask questions, or worse give any rumours Valeria might start spreading as revenge any credence. Getting rid of them, and all his other lingerie would be one of the first things he did when he got home, but he needed to be careful to dispose of them unnoticed. After that he would really be free he thought as he finished getting dressed and went straight to his dorm to go and do just that, not even considering going to Valeria to put that horrid cage back on like she had demanded of him.
Valeria saw him turn just around the corner as she left the girl’s locker room. It was clear that Jake wasn’t planning to do as she had asked, it had been expected after the chewing out he had given her. Still it was good she saw he actually followed through on his word and walked away, it meant she didn’t have to stick around for the off chance he would have changed his mind. His words, despite all the names he had called her hadn’t phased her one bit. Instead she had been looking forward to making him see just how badly he had screwed up? He would pay for every last one of those words and she was loving it. Certainly some of the video’s she had of him would change his mind and make him agree to putting that cage back on for the sake of keeping his secret, after all she did warn him earlier that he should expect punishment if he was naughty.
Humming a merry tune Valeria made her way straight to Jake’s dorm, after all she did have a feeling like Jake would do some real damage to what part of a feminine wardrobe he already had. While it would be easy to force him to replace every last item, it would be nothing more than a waste of money and cute clothes so it was better to prevent that all together. It was simply easier that way, besides it left more budget for other fun things as she didn’t want to bankrupt him either even if she wanted him to spend a lot of spare cash on further feminising himself in the future. Having him as her caged sissy toy was just too much fun so she definitely wanted to push that further.
Jake had only been at his dorm for a few short moments, barely having been able to do anything but throw the panties he had worn today out of his bag, when there was a loud knock on the door. “Babe, you didn’t show up at the toilets like I asked, not that I expected it after how rude you were. We need to talk right now. Trust me, you really don’t want to skip this talk if you know what is good for you.” Valeria spoke loud and ominously, figuring Jake wouldn’t just let her in because she wanted to talk. It seemed to have worked as a few moments later the door was slowly opened by a reluctant and angry looking Jake.
She could see that he was about to go on another cursing rant like he had been in the bathrooms, but she quickly nipped that in the butt, pressing a finger hard into his chest as a warning as she pushed her way into the dorm room. “Weigh your next words very carefully panty lover cause you are already in enough trouble as it is.” Valeria warned ominously showing no fear of the taller, stronger soccer captain that wasn’t pleased with her at all. She just kept up that dominant flair she had been gaining confidence in over the past weeks, and much to her joy it seemed to work on some level. Jake hesitated and actually let her pass. His was very used to bending to Valeria’s will by now and after a couple of weeks, it was hard not to cave a little when she was so confidently threatening him.
He didn’t like the direction this was taking one bit, he shouldn’t have let Valeria in. He reminded himself that she had no power over him anymore, nothing more than what he gave her and he wanted her to leave. Still there was a lot more hesitance then there had been in that bathroom when the cage had finally come off. Valeria’s smiling confidence throughout all of this was hugely unsettling, it made him question whether he might have overlooked something, but he shook those thoughts. He had thought about this long and hard and there was nothing but words Valeria could use against him, words that she couldn’t prove and would be easily denied. He was pissed that Valeria had casually set down on his bed like she owned the place, but he would change that right here and now. “Get out of my fucking dorm right now bitch, we are finished, you have no control over me anymore.” He spoke firmly, yet holding back a little more already as Valeria just kept on smiling, making no attempts to get up. Instead she laughed and shook her head a little, making a tsking sound.
“Really Jake? Again? You just don’t learn do you, and I did so warn you about weighing your words carefully, I really thought you were smarter than this. Or are you just insulting my intelligence, do you think that I have nothing but rumours on you anymore now that I was as dumb as to let you out of that pretty cock cage? Do you really think the idea that you might refuse to put it back on wouldn’t have occurred to me? That I would just be okay with that and try to just bluff you back into that cage?” Valeria asked with a laugh as she watched Jake’s face grow more worried with every question.
“What the hell are you talking about? Do you have anything on me? What the hell could you possibly have on me?” He asked not nearly as confident in himself anymore. He knew Valeria wasn’t stupid, but maybe she had been naïve? Maybe she had just overestimated how much control she had over him, after all he had been acting pretty wimpy up until she took off that cage. Valeria couldn’t possibly have anything on him right? No she had to be bluffing. She must have realised that she screwed up only to now try to bluff him back under her thumb.
“Why don’t you be a good sissy for a moment and come have a look for yourself? I’m certain it will clear things up for you, I promise.” Valeria spoke in a teasing tone as she patted the bed right next to her, holding her phone in her lap with the screen turned towards that spot. She loved seeing the confidence drain from Jake’s face, confidence replaced by worry and fear that she might really have something on him and that his refusal and aggression towards Valeria might come crashing down on him in the worst ways. Her sheer cheery calmness was unsettling to him.
Jake didn’t know what to think he wanted to curse Valeria for talking to him in such a condescending way, for calling him a sissy while he was getting rid of all that bull shit. He truly wanted to believe that she was just bluffing, but she seemed so damn sure about herself. He couldn’t risk it, he needed to know and so despite making up his mind about never doing a thing Valeria had told him anymore, he did eventually sit down right next to her, a morbid curiosity controlling him. He needed to know what she meant with all her vague cryptic threats and there was only one way to find out which was to do as she said one last time and so he did.
With Jake sitting way to close to her for his comfort, like they were still a couple, Valeria turned her phone sideways and showed him the video she had prepared. The one in which she gave him pointers on how to take care of his nails and paint them. While he hadn’t wanted to learn about painting his nails in that video, it all looked extremely damning. A hint of his frilly thong was on show and he put up no fuss following Valeria’s pointers to the letters while she explained how this would help keep his stockings intact if he wanted to put them on, something he carefully did at the end of the video. The way it was cut up made it seem like he had come to his girlfriend asking for advice on how to keep his stockings from running, rather than Valeria forcing him to wear stockings and instructing him on how not to damage them.
“Isn’t this just the cutest? I bet the entire campus would love to see what a nice couple we make. I bet it isn’t often they would see a girlfriend be as supportive as I have been in her boyfriend discovering his feminine side, his very feminine side at that. You finally wouldn’t have to keep your sissy secret a secret anymore, doesn’t that just sound lovely Jake?” Valeria asked teasingly, selling the spreading of this video as if it would be a good thing for him. Like it would be a relief if his secret was out.
“I’m not a sissy Valeria, you know that, you were the one that made me paint my nails and put on those damn stockings and panties.” Jake argued in panic, his whole world felt like it was crumbling down. He knew very well how this video looked and if it got out he was screwed beyond believe, it was evidence, undeniable evidence that gave the wrong idea and would give credit to whatever lies Valeria would make up about him, it was so much worse than the potential reputation damage of not honouring a bet like this whole thing had been in the first place. All he could hope for was that Valeria would agree that it wasn’t fair and would just drop it, but whether he liked it or not he was at the mercy of her good will and after all he had just said that was terrible news.
“Oh really Jake, do I know that? I mean all I know is that you have been pretty excited to wear panties and I believe that cage gave you extra trouble as well when you put on your stockings. All I know is that I’ve stumbled upon your deepest most well kept secrets sissy. I have merely been forcing you to acknowledge your own sissy desires, confronting you with them, but I never forced you to get all hot and turned on by your lingerie. In any case I see it as my moral duty to really help you find your true sense of self, I believe your secret is the reason you often act like such an asshole, trying to overcompensate on the macho side. So I’m not just helping you, I am helping all those around me and I won’t stop because you want to go back to lying to yourself and everyone else. If you can’t agree to explore your sissy self with me as your supportive girlfriend then you will leave me no choice but to force the secret out in the open, make it impossible for you to hide from it, for example by throwing this video online.” Valeria explained loud and clear putting her own spin on how the events had happened. If Jake were to start believing he had been a sissy all along he would be so much easier to handle.
Jake could only listen to Valeria’s flawed reasoning in utter shock. He wasn’t a sissy, he knew he wasn’t, but he could bring out no argument against the fact that he had gotten turned on by that lingerie despite his shame. It didn’t make sense to him either and he felt bad enough about it, without that he knew he would never be able to convince Valeria that she had to stop what she was doing, meaning he was utterly screwed. With how determined Valeria was he knew he had to play along for damage control, to prevent the whole campus from finding out about his adventures in lingerie and chastity, about why he had been acting like such a wimp. He dreaded following Valeria’s rules again, especially after all he had said and done, but what choice did he have? Falling in line was the only way to keep this all a secret.
“I see you understand what’s going to happen Jake, so you have two options now. Either you kick me out of your room and I’ll expose you, or you get an ice pack, strip down, put this cage back on in front of me, put that key back on the anklet I’m wearing, put on a pair of your pretty panties and some of those glossy stockings you so happily bought to feel extra special. Then you can kneel right here, kiss my shoes and apologise for what you’ve said and done while asking me nicely to punish you for it, and ask nicely for my help in discovering the full extent of your sissy side.” Valeria spoke firmly with a huge smirk as the thumb of her one hand hovered over the share button on the video while her other hand held the multiple parts of the cage with the key still in the heart shaped lock from when she had taken it off a few hours earlier.
Utterly mortified Jake just stood there for a few long moments, already knowing what he had to do, but extremely reluctant to actually do it. Eventually he did find the courage however, not wanting to anger Valeria any more her reluctantly took the cage out of her hands and went to his fridge to get an icepack out of the freezer compartment. Slowly but surely he stripped naked in front of what he guessed was his girlfriend once more. He had no illusion about what kind of relationship they had though as Valeria smirked down upon him making him feel oh so embarrassed to get naked. He really couldn’t believe he was actually putting that cage on himself after just having gotten rid of it for what he had thought was once and for all. Hell he had even called for a celebration, another thing he needed to worry about as he couldn’t possibly see himself going out right now. How would his friends react knowing he got back with Valeria so soon, going back to being a wimp for her after he had made such a big fuss about breaking up with her. It was devastating, but right now the worst thing was how he had to shrink his smooth cock down with that uncomfortable ice.
With his cock as small as the ice would get it and under the amused shameful giggling of Valeria, Jake locked the snug cage back onto his cock. Clicking the lock shut himself was way more devastating than it had been to be tricked into this damn thing, or cuffed when it happened. It got even worse as he ended up fumbling with the delicate ankle chain, only to get it loose, get the small key on it and get it locked back around Valeria’s ankle, literally submitting his cock back to her foot.
As if all that wasn’t embarrassing enough, he was then forced to get back into that shameful lingerie, a pastel green pair of those horribly frilly thongs, the first pair he found, and a pair of those delicate sheer nude stockings with their slight shine to them. Knowing that he was screwed even more if he ruined them, he ended up being very careful with the garment once more as Valeria laughed at him. She laughed even harder when he let out a loud groan, his cock instantly reacting to the sensual feel of the satin and the nylons only to be kept down by that horrid cage. “See sissy, my point exactly, you might say you are not a sissy, but your cock betrays you.” She grinned rubbing more salt in the wound.
All the confidence he had regained with his freedom quickly vanished and then some as he realised that he had to put up with this until Valeria decided otherwise, something he doubted she would do any time soon, he was so fucking screwed, but right now he could only hope not to screw things up any more as he felt mortified and submissive bowing his head to his triumphant girlfriend of sorts, kissing the tips of her sneakers, his eyes on the key to his cock around her ankles before looking up at her. “I would like to offer you my sincerest apologies for how I have been acting the last few hours Miss, could you please forgive me, and punish me for my indiscretions? I realise now that I was wrong, and I can only hope you’ll agree when I ask you to please help me discover the full extent of my sissy side.” Jake spoke humbly, cringing at every word especially when he asked her to take this whole thing further. It was horrible. Now all he could do was wait, his heart pounding in his chest as Valeria seemed in no hurry at all, just sitting there, savouring the power she had over him as she made him wait for the judgement she would pass, this was so much fun.
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